Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof

ABSTRACT

Provided are a compound of Formula (1) for use in an organic electronic element and capable of improving the luminous efficiency, stability and lifespan of the organic electronic element, an organic electronic element employing the compound, and an electronic device thereof.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a Continuation-in-Part of U.S. patent applicationSer. No. 17/212,886, filed on Mar. 25, 2021, which was a Continuation ofU.S. patent application Ser. No. 17/096,790, filed on Nov. 12, 2020, nowU.S. Pat. No. 11,063,226, issued on Jul. 13, 2021, which claims priorityto and the benefit of Korean Patent Application No. 10-2020-0139441,filed on Oct. 26, 2020, the disclosure of which is incorporated hereinby reference in its entirety.

BACKGROUND Technical Field

The present invention relates to a compound for an organic electronicelement, an organic electronic element using the same, and an electronicdevice thereof.

Background Art

In general, organic light emitting phenomenon refers to a phenomenonthat converts electric energy into light energy by using an organicmaterial. An organic electronic element using an organic light emittingphenomenon usually has a structure including an anode, a cathode, and anorganic material layer interposed therebetween. Here, in order toincrease the efficiency and stability of the organic electronic element,the organic material layer is often composed of a multi-layeredstructure composed of different materials, and for example, may includea hole injection layer, a hole transport layer, an emitting layer, anelectron transport layer, an electron injection layer and the like.

A material used as an organic material layer in an organic electronicelement may be classified into a light emitting material and a chargetransport material, such as a hole injection material, a hole transportmaterial, an electron transport material, an electron injection materialand the like depending on its function. And the light emitting materialcan be classified into a high molecular weight type and a low molecularweight type according to the molecular weight, and according to thelight emission mechanism, it can be classified into a fluorescentmaterial derived from a singlet excited state of an electron and aphosphorescent material derived from a triplet excited state of anelectron. Also, the light emitting material may be divided into blue,green, and red light emitting materials and yellow and orange lightemitting materials necessary for realizing a better natural coloraccording to the emission color.

However, when only one material is used as a light emitting material,due to intermolecular interaction, the maximum emission wavelengthshifts to a longer wavelength, and there are problems in that the colorpurity is lowered or the device efficiency is reduced due to theemission attenuation effect, therefore in order to increase color purityand increase luminous efficiency through energy transfer, a host/dopantsystem may be used as a light emitting material. The principle is thatwhen a small amount of a dopant having a smaller energy band gap thanthat of the host forming the emitting layer is mixed in the emittinglayer, excitons generated in the emitting layer are transported to thedopant to emit light with high efficiency. At this time, since thewavelength of the host moves to the wavelength band of the dopant, lighthaving a desired wavelength can be obtained according to the type ofdopant used.

Currently, the portable display market is a large-area display, and thesize thereof is increasing, and thus, more power consumption than thepower consumption required for the existing portable display isrequired. Therefore, power consumption has become a very importantfactor for a portable display having a limited power supply such as abattery, and the problem of efficiency and lifespan must also be solved.

Efficiency, lifespan, and driving voltage are related to each other, andwhen the efficiency is increased, the driving voltage is relativelydecreased, and as the driving voltage is decreased, crystallization oforganic materials due to Joule heating generated during drivingdecreases, and consequently, the lifespan tends to increase. However,the efficiency cannot be maximized simply by improving the organicmaterial layer. This is because, when the energy level and T1 valuebetween each organic material layer, and the intrinsic properties(mobility, interfacial properties, etc.) of materials are optimallycombined, long lifespan and high efficiency can be achieved at the sametime.

Therefore, while delaying the penetration and diffusion of metal oxidefrom the anode electrode (ITO) into the organic layer, which is one ofthe causes of shortening the lifespan of the organic electronic element,it should have stable characteristics against Joule heating generatedduring device driving, and OLED devices are mainly formed by adeposition method, and it is necessary to develop a material that canwithstand a long time during deposition, that is, a material with strongheat resistance.

In other words, in order to fully exhibit the excellent characteristicsof an organic electronic element, the material constituting the organicmaterial layer in the device, such as a hole injection material, a holetransport material, a light emitting material, an electron transportmaterial, an electron injection material, etc., is supported by a stableand efficient material and should take precedence, but the developmentof a stable and efficient organic material layer material for an organicelectronic device has not yet been sufficiently made. Therefore, thedevelopment of new materials is continuously required, and inparticular, the development of a host material for the emitting layer isurgently required.

DETAILED DESCRIPTION OF THE INVENTION Summary

In order to solve the problems of the above-mentioned background art,the present invention has revealed a compound having a novel structure,and when this compound is applied to an organic electronic element, ithas been found that the luminous efficiency, stability and lifespan ofthe device can be significantly improved.

Accordingly, an object of the present invention is to provide a novelcompound, an organic electronic element using the same, and anelectronic device thereof.

Technical Solution

The present invention provides a compound represented by Formula (1):

In another aspect, the present invention provides an organic electronicelement comprising the compound represented by Formula (1) and anelectronic device thereof.

Effects of the Invention

By using the compound according to the present invention, high luminousefficiency, low driving voltage and high heat resistance of the devicecan be achieved, and color purity and lifespan of the device can begreatly improved.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 to FIG. 3 each illustrate an exemplary view of an organicelectroluminescent device according to the present invention.

The numbers in the drawings indicates: 100, 200, 300: organic electronic110: the first electrode element 120: hole injection layer 130: holetransport layer 140: emitting layer 150: electron transport layer 160:electron injection layer 170: second electrode 180: light efficiencyenhancing Layer 210: buffer layer 220: emitting-auxiliary layer 320:first hole injection layer 330: first hole transport layer 340: firstemitting layer 350: first electron transport layer 360: first chargegeneration layer 361: second charge generation layer 420: second holeinjection layer 430: second hole transport layer 440: second emittinglayer 450: second electron transport layer CGL: charge generation layerST1: first stack ST2: second stack

DETAILED DESCRIPTION

Hereinafter, some embodiments of the present invention will be describedin detail. Further, in the following description of the presentinvention, a detailed description of known functions and configurationsincorporated herein will be omitted when it may make the subject matterof the present invention rather unclear.

In addition, terms, such as first, second, A, B, (a), (b) or the likemay be used herein when describing components of the present invention.Each of these terminologies is not used to define an essence, order orsequence of a corresponding component but used merely to distinguish thecorresponding component from other component(s). It should be noted thatif a component is described as being “connected”, “coupled”, or“connected” to another component, the component may be directlyconnected or connected to the other component, but another component maybe “connected”, “coupled” or “connected” between each component.

As used in the specification and the accompanying claims, unlessotherwise stated, the following is the meaning of the term as follows.

Unless otherwise stated, the term “halo” or “halogen”, as used herein,includes fluorine, bromine, chlorine, or iodine.

Unless otherwise stated, the term “alkyl” or “alkyl group”, as usedherein, has a single bond of 1 to 60 carbon atoms, and means saturatedaliphatic functional radicals including a linear alkyl group, a branchedchain alkyl group, a cycloalkyl group (alicyclic), an cycloalkyl groupsubstituted with a alkyl or an alkyl group substituted with acycloalkyl.

Unless otherwise stated, the term “alkenyl” or “alkynyl”, as usedherein, has double or triple bonds of 2 to 60 carbon atoms, but is notlimited thereto, and includes a linear or a branched chain group.

Unless otherwise stated, the term “cycloalkyl”, as used herein, meansalkyl forming a ring having 3 to 60 carbon atoms, but is not limitedthereto.

Unless otherwise stated, the term “alkoxyl group”, “alkoxy group” or“alkyloxy group”, as used herein, means an oxygen radical attached to analkyl group, but is not limited thereto, and has 1 to 60 carbon atoms.

Unless otherwise stated, the term “aryloxyl group” or “aryloxy group”,as used herein, means an oxygen radical attached to an aryl group, butis not limited thereto, and has 6 to 60 carbon atoms.

The terms “aryl group” and “arylene group” used in the present inventionhave 6 to 60 carbon atoms, respectively, unless otherwise specified, butare not limited thereto. In the present invention, an aryl group or anarylene group means a single ring or multiple ring aromatic, andincludes an aromatic ring formed by an adjacent substituent joining orparticipating in a reaction.

For example, the aryl group may be a phenyl group, a biphenyl group, afluorenyl group, or a spirofluorene group.

The prefix “aryl” or “ar” means a radical substituted with an arylgroup. For example, an arylalkyl may be an alkyl substituted with anaryl, and an arylalkenyl may be an alkenyl substituted with aryl, and aradical substituted with an aryl has a number of carbon atoms as definedherein.

Also, when prefixes are named subsequently, it means that substituentsare listed in the order described first. For example, an arylalkoxymeans an alkoxy substituted with an aryl, an alkoxylcarbonyl means acarbonyl substituted with an alkoxyl, and an arylcarbonylalkenyl alsomeans an alkenyl substituted with an arylcarbonyl, wherein thearylcarbonyl may be a carbonyl substituted with an aryl.

Unless otherwise stated, the term “heterocyclic group”, as used herein,contains one or more heteroatoms, but is not limited thereto, has 2 to60 carbon atoms, includes any one of a single ring or multiple ring, andmay include heteroaliphadic ring and heteroaromatic ring. Also, theheterocyclic group may also be formed in conjunction with an adjacentgroup.

Unless otherwise stated, the term “heteroatom”, as used herein,represents at least one of N, O, S, P, or Si.

Also, the term “heterocyclic group” may include a ring including SO₂instead of carbon consisting of cycle. For example, “heterocyclic group”includes the following compound.

Unless otherwise stated, the term “fluorenyl group” or “fluorenylenegroup”, as used herein, means a monovalent or divalent functional group,in which R, R′ and R″ are all hydrogen in the following structures, andthe term “substituted fluorenyl group” or “substituted fluorenylenegroup” means that at least one of the substituents R, R′, R″ is asubstituent other than hydrogen, and include those in which R and R′ arebonded to each other to form a spiro compound together with the carbonto which they are bonded.

The term “spiro compound”, as used herein, has a ‘spiro union’, and aspiro union means a connection in which two rings share only one atom.At this time, atoms shared in the two rings are called ‘spiro atoms’,and these compounds are called ‘monospiro-’, ‘di-spiro-’ and‘tri-spiro-’, respectively, depending on the number of spiro atoms in acompound.

Unless otherwise stated, the term “aliphatic”, as used herein, means analiphatic hydrocarbon having 1 to 60 carbon atoms, and the term“aliphatic ring”, as used herein, means an aliphatic hydrocarbon ringhaving 3 to 60 carbon atoms.

Unless otherwise stated, the term “ring”, as used herein, means analiphatic ring having 3 to 60 carbon atoms, or an aromatic ring having 6to 60 carbon atoms, or a hetero ring having 2 to 60 carbon atoms, or afused ring formed by the combination of them, and includes a saturatedor unsaturated ring.

Other hetero compounds or hetero radicals other than the above-mentionedhetero compounds include, but are not limited thereto, one or moreheteroatoms.

Also, unless expressly stated, as used herein, “substituted” in the term“substituted or unsubstituted” means substituted with one or moresubstituents selected from the group consisting of deuterium, halogen,an amino group, a nitrile group, a nitro group, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxyl group, a C₁-C₂₀ alkylamine group, a C₁-C₂₀ alkylthiopengroup, a C₆-C₂₀ arylthiopen group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀alkynyl group, a C₃-C₂₀ cycloalkyl group, a C₆-C₂₀ aryl group, a C₆-C₂₀aryl group substituted by deuterium, a C₈-C₂₀ arylalkenyl group, asilane group, a boron group, a germanium group, and a C₂-C₂₀heterocyclic group, but is not limited to these substituents.

Also, unless there is an explicit explanation, the formula used in thepresent invention is the same as the definition of the substituent bythe exponent definition of the following formula.

Here, when a is an integer of zero, the substituent IV is absent, when ais an integer of 1, the sole substituent IV is linked to any one of thecarbon constituting the benzene ring, when a is an integer of 2 or 3,each is combined as follows, where IV may be the same or different fromeach other, when a is an integer of 4 to 6, it is bonded to the carbonof the benzene ring in a similar manner, while the indication of thehydrogen bonded to the carbon forming the benzene ring is omitted.

Hereinafter, a compound according to an aspect of the present inventionand an organic electronic element including the same will be described.

The present invention provides a compound represented by Formula (1):

wherein:1) Ar₁ and Ar₂ are each independently of a C₆-C₁₈ aryl group; or aC₆-C₁₈ aryl group substituted with deuterium;2) R¹, R², R³, R⁴, R⁵ and R⁶ are the same or different from each other,and independently of each other are hydrogen or deuterium;3) a is an integer of 0 to 7, b is an integer of 0 to 6.

Also, the present invention provides a compound in which Formula (1) isrepresented by Formula (1-1) or Formula (1-2):

Wherein Ar₁, Ar₂, R¹, R², R³, R⁴, R⁵, R⁶, a and b are the same asdefined above.

Also, the present invention provides a compound in which Ar₁ or Ar₂ isrepresented by any one of the above compounds:

wherein1) R¹, R² and a are the same as defined above,2) a′ and b′ are independently of each other an integer from 0 to 5, a″is an integer from 0 to 4,3) * means the bonding position.

Also, the present invention provides a compound having a reorganizationenergy value of less than 0.190 of the compound represented by Formula(1).

Also, the present invention provides a compound having a reorganizationenergy value of 0.155 to 0.170 of the compound represented by Formula(1).

Also, the present invention provides a compound in which the compoundrepresented by Formula (1) is represented by any one of the followingcompounds P-1 to P-64:

Referring to FIG. 1, the organic electronic element (100) according tothe present invention includes a first electrode (110), a secondelectrode (170), and an organic material layer including a singlecompound or 2 or more compounds represented by Formula (1) between thefirst electrode (110) and the second electrode (170). In this case, thefirst electrode (110) may be an anode, and the second electrode (170)may be a cathode. In the case of an inverted type, the first electrodemay be a cathode and the second electrode may be an anode.

The organic material layer may sequentially include a hole injectionlayer (120), a hole transport layer (130), an emitting layer (140), anelectron transport layer (150), and an electron injection layer (160) onthe first electrode (110). In this case, the remaining layers except forthe emitting layer (140) may not be formed. It may further include ahole blocking layer, an electron blocking layer, an emitting auxiliarylayer (220), a buffer layer (210), etc. and the electron transport layer(150) and the like may serve as a hole blocking layer. (See FIG. 2)

Also, the organic electronic element according to an embodiment of thepresent invention may further include a protective layer or a lightefficiency enhancing layer (180). The light efficiency enhancing layermay be formed on one of both surfaces of the first electrode not incontact with the organic material layer or on one of both surfaces ofthe second electrode not in contact with the organic material layer. Thecompound according to an embodiment of the present invention applied tothe organic material layer may be used as a host or dopant of the holeinjection layer (120), the hole transport layer (130), the emittingauxiliary layer (220), electron transport auxiliary layer, the electrontransport layer (150), and an electron injection layer (160), theemitting layer (140) or as a material for the light efficiency enhancinglayer. Preferably, for example, the compound according to Formula (1) ofthe present invention may be used as a host material of the emittinglayer, a hole blocking layer or an electron transport layer.

The organic material layer may include 2 or more stacks including a holetransport layer, an emitting layer and an electron transport layersequentially formed on the anode, further include a charge generationlayer formed between the 2 or more stacks (see FIG. 3).

Otherwise, even with the same core, the band gap, electricalcharacteristics, interface characteristics, etc. may vary depending onwhich position the substituent is bonded to, therefore the choice ofcore and the combination of sub-substituents bound thereto are also veryimportant, and in particular, when the optimal combination of energylevels and T1 values and unique properties of materials (mobility,interfacial characteristics, etc.) of each organic material layer isachieved, a long lifespan and high efficiency can be achieved at thesame time. The organic electroluminescent device according to anembodiment of the present invention may be manufactured using a PVD(physical vapor deposition) method. For example, depositing a metal or ametal oxide having conductivity or an alloy thereof on a substrate toform an anode, and after forming an organic material layer including thehole injection layer (120), the hole transport layer (130), the emittinglayer (140), the electron transport layer (150) and the electroninjection layer (160) thereon, it can be prepared by depositing amaterial that can be used as a cathode thereon.

Also, in the present invention, the organic material layer is formed byany one of a spin coating process, a nozzle printing process, an inkjetprinting process, a slot coating process, a dip coating process, and aroll-to-roll process, and the organic material layer provides an organicelectric element comprising the compound as an electron transportmaterial.

As another specific example, the same or different compounds of thecompound represented by Formula (1) are mixed and used in the organicmaterial layer.

Also, the present invention provides an emitting layer compositioncomprising the compound represented by Formula (1), and provides anorganic electronic element comprising the emitting layer.

Also, the present invention provides a hole blocking layer compositioncomprising the compound represented by Formula (1), and provides anorganic electronic element comprising the hole blocking layer.

Also, the present invention provides an electron transport layercomposition comprising the compound represented by Formula (1), andprovides an organic electronic element comprising the electron transportlayer.

Also, the present invention provides an electronic device comprising adisplay device including the organic electronic element; and a controlunit for driving the display device;

In another aspect, the organic electronic element is at least one of anorganic electroluminescent device, an organic solar cell, an organicphotoreceptor, an organic transistor, and a device for monochromatic orwhite lighting. At this time, the electronic device may be a current orfuture wired/wireless communication terminal, and covers all kinds ofelectronic devices including mobile communication terminals such asmobile phones, a personal digital assistant (PDA), an electronicdictionary, a point-to-multipoint (PMP), a remote controller, anavigation unit, a game player, various kinds of TVs, and various kindsof computers.

Hereinafter, a synthesis example of the compound represented by Formula(1) of the present invention and a manufacturing example of an organicelectronic element of the present invention will be described in detailwith reference to Examples, but the present invention is not limited tothe following Examples.

Synthesis Examples

The compound (final products) represented by Formula (1) according tothe present invention is synthesized by reacting Sub 1 and Sub 2 asshown in Scheme 1 below, but is not limited thereto.

I. Synthesis of Sub 1

Sub 1 of Reaction Scheme 1 may be synthesized by the reaction route ofReaction Scheme 2 below, but is not limited thereto.

Synthesis examples of specific compounds belonging to Sub 1 are asfollows.

1. Synthesis Example Sub 1-1

(1) Synthesis of Sub 1-1b

naphthalen-2-ylboronic acid (23.9 g, 0.14 mol), Pd(PPh₃)₄ (6.1 g, 0.005mol), NaOH (21 g, 0.52 mol), THF (350 mL) and water (115 mL) were addedto Sub 1-1a (50 g, 0.17 mol), and the reaction was conducted at 70° C.for 6 hours.

When the reaction is completed, the temperature of the reactant iscooled to room temperature, and the solvent is removed. Then, theconcentrated reactant was separated using a silica gel column orrecrystallization method to obtain 48 g (82.4%) of the product Sub 1-1b.

(2) Synthesis of Sub 1-1

Sub 1-1b (30 g, 0.09 mol),1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (29.7 g,0.09 mol), Pd(PPh₃)₄ (3.1 g, 0.003 mol), NaOH (10.8 g, 0.27 mol), THF(180 mL) and water (60 mL) were added, and the reaction was carried outat 70° C. for 6 hours. When the reaction is completed, the temperatureof the reactant is cooled to room temperature, and the solvent isremoved. Then, the concentrated reactant was separated using a silicagel column or recrystallization method to obtain 33 g (80.4%) of theproduct Sub 1-33.

2. Synthesis Example Sub 1-5

(1) Synthesis of Sub 1-5b

(naphthalen-2-yl-d7)boronic acid (24.5 g, 0.14 mol), Pd(PPh₃)₄ (4.8 g,0.004 mol), NaOH (16.4 g, 0.41 mol), THF (280 mL) and water (90 mL) wereadded to Sub 1-5a (40 g, 0.14 mol), and the reaction was conducted at70° C. for 6 hours. When the reaction was completed, 35 g (73.8%) of theproduct Sub 1-5b was obtained by using the separation method of Sub 1-1bdescribed above.

(2) Synthesis of Sub 1-5

Sub 1-5b (35 g, 0.10 mol),1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (33.4 g,0.10 mol), Pd(PPh₃)₄ (3.5 g, 0.003 mol), NaOH (12.1 g, 0.30 mol), THF(200 mL) water (70 mL) were added, and the reaction was carried out at70° C. for 6 hours. When the reaction is completed, the temperature ofthe reactant is cooled to room temperature, and the solvent is removed.When the reaction was completed, 35 g (73.8%) of the product Sub 1-5 wasobtained by using the separation method for Sub 1-1 described above.

3. Synthesis Example of Sub 1-7

(1) Synthesis of Sub 1-1b

48 g (82.4%) of the product Sub 1-1b was obtained by using the synthesismethod of Sub 1-1b described above.

(2) Synthesis of Sub 1-7

Sub 1-1b (30 g, 0.09 mol),1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (29.7 g,0.09 mol), Pd(PPh₃)₄ (3.1 g, 0.003 mol), NaOH (10.8 g, 0.27 mol), THF(180 mL) and water (60 mL) were added, and the reaction was carried outat 70° C. for 6 hours. When the reaction was completed, 35 g (85.2%) ofthe product Sub 1-7 was obtained by using the separation method for Sub1-1 described above.

4. Synthesis Example of Sub 1-9

(1) Synthesis of Sub 1-9b

naphthalen-2-ylboronic acid (23.4 g, 0.14 mol), Pd(PPh₃)₄ (4.8 g, 0.004mol), NaOH (16.4 g, 0.41 mol), THF (280 mL) and water (90 mL) were addedto Sub 1-5a (40 g, 0.14 mol), and the reaction was conducted at 70° C.for 6 hours. When the reaction was completed, 38 g (81.8%) of theproduct Sub 1-9b was obtained by using the separation method of Sub 1-1bdescribed above.

(2) Synthesis of Sub 1-9

Sub 1-9b (38 g, 0.11 mol),1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (37 g, 0.11mol), Pd(PPh₃)₄ (3.9 g, 0.003 mol), NaOH (13.5 g, 0.34 mol), THF (230mL) and water (70 mL) were added, and the reaction was carried out at70° C. for 6 hours. When the reaction was completed, 42 g (81.1%) of theproduct Sub 1-9 was obtained by using the separation method for Sub 1-1described above.

Meanwhile, the compound belonging to Sub 1 may be the followingcompounds, but is not limited thereto, and Table 1 below shows FD-MS(Field Desorption-Mass Spectrometry) values of the compounds belongingto Sub 1-1.

TABLE 1 compound FD-MS Sub 1-1 m/z = 456.23(C₃₂H₂₉BO₂ = 456.39) Sub 1-2m/z = 463.27(C₃₂H₂₂D₇BO₂ = 463.43) Sub 1-3 m/z = 462.26(C₃₂H₂₃D₆BO₂ =462.43) Sub 1-4 m/z = 460.25(C₃₂H₂₅D₄BO₂ = 460.42) Sub 1-5 m/z =469.31(C₃₂H₁₆D₁₃BO₂ = 469.47) Sub 1-6 m/z = 458.24(C₃₂H₂₇D₂BO₂ = 458.4)Sub 1-7 m/z = 456.23(C₃₂H₂₉BO₂ = 456.39) Sub 1-8 m/z =467.3(C₃₂H₁₈D₁₁BO₂ = 467.46) Sub 1-9 m/z = 462.26(C₃₂H₂₃D₆BO₂ = 462.43)Sub 1-10 m/z = 458.24(C₃₂H₂₇D₂BO₂ = 458.4) Sub 1-11 m/z =463.27(C₃₂H₂₂D₇BO₂ = 463.43)

Meanwhile, the compound belonging to Sub 2 may be a compound as follows,but is not limited thereto, and Table 2 below shows FieldDesorption-Mass Spectrometry (FD-MS) values of the compound belonging toSub 2.

TABLE 2 compound FD-MS Sub2-1 m/z = 267.06(C₁₅H₁₀ClN₃ = 267.72) Sub2-2m/z = 317.07(C₁₉H₁₂ClN₃ = 317.78) Sub2-3 m/z = 317.07(C₁₉H₁₂ClN₃ =317.78) Sub2-4 m/z = 343.09(C₂₁H₁₄ClN₃ = 343.81) Sub2-5 m/z =343.09(C₂₁H₁₄ClN₃ = 343.81) Sub2-6 m/z = 343.09(C₂₁H₁₄ClN₃ = 343.81)Sub2-7 m/z = 393.1(C₂₅H₁₆ClN₃ = 393.87) Sub2-8 m/z = 393.1(C₂₅H₁₆ClN₃ =393.87) Sub2-9 m/z = 393.1(C₂₅H₁₆ClN₃ = 393.87) Sub2-10 m/z =419.12(C₂₇H₁₈ClN₃ = 419.91) Sub2-11 m/z = 367.09(C₂₃H₁₄ClN₃ = 367.84)Sub2-12 m/z = 367.09(C₂₃H₁₄ClN₃ = 367.84) Sub2-13 m/z =367.09(C₂₃H₁₄ClN₃ = 367.84) Sub2-14 m/z = 272.09(C₁₅H₅D₅ClN₃ = 272.75)Sub2-15 m/z = 348.12(C₂₁H₉D₅ClN₃ = 348.84) Sub2-16 m/z =270.08(C₁₅H₇D₃ClN₃ = 270.73) Sub2-17 m/z = 367.09(C₂₃H₁₄ClN₃ = 367.84)Sub2-18 m/z = 367.09(C₂₃H₁₄ClN₃ = 367.84) Sub2-19 m/z =367.09(C₂₃H₁₄ClN₃ = 367.84) Sub2-20 m/z = 393.1(C₂₅H₁₆ClN₃ = 393.87)Sub2-21 m/z = 393.1(C₂₅H₁₆ClN₃ = 393.87) Sub2-22 m/z = 393.1(C₂₅H₁₆ClN₃= 393.87) Sub2-23 m/z = 393.1(C₂₅H₁₆ClN₃ = 393.87) Sub2-24 m/z =417.1(C₂₇H₁₆ClN₃ = 417.9) Sub2-25 m/z = 417.1(C₂₇H₁₆ClN₃ = 417.9)Sub2-26 m/z = 443.12(C₂₉H₁₈ClN₃ = 443.93) Sub2-27 m/z =469.13(C₃₁H₂₀ClN₃ = 469.97) Sub2-28 m/z = 419.12(C₂₇H₁₈ClN₃ = 419.91)Sub2-29 m/z = 419.12(C₂₇H₁₈ClN₃ = 419.91) Sub2-30 m/z =419.12(C₂₇H₁₈ClN₃ = 419.91) Sub2-31 m/z = 419.12(C₂₇H₁₈ClN₃ = 419.91)Sub2-32 m/z = 469.13(C₃₁H₂₀ClN₃ = 469.97) Sub2-33 m/z =469.13(C₃₁H₂₀ClN₃ = 469.97) Sub2-34 m/z = 469.13(C₃₁H₂₀ClN₃ = 469.97)Sub2-35 m/z = 419.12(C₂₇H₁₈ClN₃ = 419.91) Sub2-36 m/z =467.12(C₃₁H₁₈ClN₃ = 467.96) Sub2-37 m/z = 467.12(C₃₁H₁₈ClN₃ = 467.96)Sub2-38 m/z = 322.1(C₁₉H₇D₅ClN₃ = 322.81) Sub2-39 m/z =277.12(C₁₅D₁₀ClN₃ = 277.78) Sub2-40 m/z = 443.12(C₂₉H₁₈ClN₃ = 443.93)Sub2-41 m/z = 469.13(C₃₁H₂₀ClN₃ = 469.97) Sub2-42 m/z =423.14(C₂₇H₁₄D₄ClN₃ = 423.94) Sub2-43 m/z = 469.13(C₃₁H₂₀ClN₃ = 469.97)

II. Synthesis of Final Products 1. Synthesis Example of P-1

Sub 1-1 (20 g, 0.04 mol), Sub 2-1 (11.7 g, 0.04 mol), Pd(PPh₃)₄ (1.5 g,0.001 mol), NaOH (5.3 g, 0.13 mol), THF (90 mL) and water (30 mL) wereadded, and the reaction was conducted at 70° C. for 6 hours. When thereaction is completed, the temperature of the reactant is cooled to roomtemperature, and the reaction solvent is removed. Then, the concentratedreactant was separated using a silica gel column or recrystallizationmethod to obtain 22 g (89.4%) of product P-1.

2. Synthesis Example of P-3

Sub 1-1 (20 g, 0.04 mol), Sub 2-3 (13.9 g, 0.04 mol), Pd(PPh₃)₄ (1.5 g,0.001 mol), NaOH (5.3 g, 0.13 mol), THF (90 mL) and water (30 mL) wereadded, and the reaction was conducted at 70° C. for 6 hours. When thereaction was completed, 23 g (85.8%) of the product P-3 was obtained byusing the separation method for P-1 described above.

3. Synthesis Example of P-10

Sub 1-1 (33 g, 0.07 mol), Sub 2-28 (30.3 g, 0.07 mol), Pd(PPh₃)₄ (2.5 g,0.002 mol), NaOH (8.7 g, 0.22 mol), THF (90 mL) and water (50 mL) wereadded, and the reaction was conducted at 70° C. for 6 hours. When thereaction was completed, 46 g (89.1%) of the product P-10 was obtained byusing the separation method for P-1 described above.

4. Synthesis Example of P-25

Sub 1-2 (30 g, 0.06 mol), Sub 2-1 (17.3 g, 0.06 mol), Pd(PPh₃)₄ (2.2 g,0.002 mol), NaOH (7.8 g, 0.19 mol), THF (130 mL) and water (40 mL) wereadded, and the reaction was conducted at 70° C. for 6 hours. When thereaction was completed, 30 g (81.5%) of the product P-25 was obtained byusing the separation method for P-1 described above.

5. Synthesis Example of P-29

Sub 1-2 (35 g, 0.08 mol), Sub 2-14 (20.6 g, 0.08 mol), Pd(PPh₃)₄ (2.6 g,0.002 mol), NaOH (9.1 g, 0.23 mol), THF (150 mL) and water (50 mL) wereadded, and the reaction was conducted at 70° C. for 6 hours. When thereaction was completed, 40 g (92.3%) of the product P-29 was obtained byusing the separation method for P-1 described above.

6. Synthesis Example of P-34

Sub 1-7 (30 g, 0.07 mol), Sub 2-2 (20.9 g, 0.07 mol), Pd(PPh₃)₄ (2.3 g,0.002 mol), NaOH (7.9 g, 0.20 mol), THF (130 mL) and water (40 mL) wereadded, and the reaction was conducted at 70° C. for 6 hours. When thereaction was completed, 32 g (79.6%) of the product P-34 was obtained byusing the separation method for P-1 described above.

7. Synthesis Example of P-51

Sub 1-7 (20 g, 0.04 mol), Sub 2-12 (16.1 g, 0.04 mol), Pd(PPh₃)₄ (1.5 g,0.001 mol), NaOH (5.3 g, 0.13 mol), THF (90 mL) and water (30 mL) wereadded, and the reaction was conducted at 70° C. for 6 hours. When thereaction was completed, 26 g (89.7%) of the product P-51 was obtained byusing the separation method for P-1 described above.

8. Synthesis Example of P-62

Sub 1-9 (15 g, 0.03 mol), Sub 2-14 (8.8 g, 0.03 mol), Pd(PPh₃)₄ (1.1 g,0.001 mol), NaOH (3.9 g, 0.10 mol), THF (65 mL) and water (20 mL) wereadded, and the reaction was conducted at 70° C. for 6 hours. When thereaction was completed, 15 g (80.8%) of the product P-62 was obtained byusing the separation method for P-1 described above.

Meanwhile, FD-MS values of compounds P-1 to P-64 of the presentinvention prepared according to the above synthesis examples are shownin Table 3 below.

TABLE 3 compound FD-MS P-1 m/z = 561.22(C₄₁H₂₇N₃ = 561.69) P-2 m/z =611.24(C₄₅H₂₉N₃ = 611.75) P-3 m/z = 611.24(C₄₅H₂₉N₃ = 611.75) P-4 m/z =661.25(C₄₉H₃₁N₃ = 661.81) P-5 m/z = 661.25(C₄₉H₃₁N₃ = 661.81) P-6 m/z =637.25(C₄₇H₃₁N₃ = 637.79) P-7 m/z = 637.25(C₄₇H₃₁N₃ = 637.79) P-8 m/z =637.25(C₄₇H₃₁N₃ = 637.79) P-9 m/z = 687.27(C₅₁H₃₃N₃ = 687.85) P-10 m/z =713.28(C₅₃H₃₅N₃ = 713.88) P-11 m/z = 713.28(C₅₃H₃₅N₃ = 713.88) P-12 m/z= 713.28(C₅₃H₃₅N₃ = 713.88) P-13 m/z = 713.28(C₅₃H₃₅N₃ = 713.88) P-14m/z = 687.27(C₅₁H₃₃N₃ = 687.85) P-15 m/z = 687.27(C₅₁H₃₃N₃ = 687.85)P-16 m/z = 763.3(C₅₇H₃₇N₃ = 763.94) P-17 m/z = 661.25(C₄₉H₃₁N₃ = 661.81)P-18 m/z = 661.25(C₄₉H₃₁N₃ = 661.81) P-19 m/z = 711.27(C₅₃H₃₃N₃ =711.87) P-20 m/z = 763.3(C₅₇H₃₇N₃ = 763.94) P-21 m/z = 661.25(C₄₉H₃₁N₃ =661.81) P-22 m/z = 687.27(C₅₁H₃₃N₃ = 687.85) P-23 m/z = 761.28(C₅₇H₃₅N₃= 761.93) P-24 m/z = 763.3(C₅₇H₃₇N₃ = 763.94) P-25 m/z =568.26(C₄₁H₂₀D₇N₃ = 568.73) P-26 m/z = 567.26(C₄₁H₂₁D₆N₃ = 567.72) P-27m/z = 616.27(C₄₅H₂₄D₅N₃ = 616.78) P-28 m/z = 641.28(C₄₇H₂₇D₄N₃ = 641.81)P-29 m/z = 573.3(C₄₁H₁₅D₁₂N₃ = 573.76) P-30 m/z = 624.32(C₄₅H₁₆D₁₃N₃ =624.83) P-31 m/z = 573.3(C₄₁H₁₅D₁₂N₃ = 573.76) P-32 m/z =646.31(C₄₇H₂₂D₉N₃ = 646.84) P-33 m/z = 561.22(C₄₁H₂₇N₃ = 561.69) P-34m/z = 611.24(C₄₅H₂₉N₃ = 611.75) P-35 m/z = 611.24(C₄₅H₂₉N₃ = 611.75)P-36 m/z = 661.25(C₄₉H₃₁N₃ = 661.81) P-37 m/z = 661.25(C₄₉H₃₁N₃ =661.81) P-38 m/z = 661.25(C₄₉H₃₁N₃ = 661.81) P-39 m/z = 687.27(C₅₁H₃₃N₃= 687.85) P-40 m/z = 711.27(C₅₃H₃₃N₃ = 711.87) P-41 m/z =687.27(C₅₁H₃₃N₃ = 687.85) P-42 m/z = 737.28(C₅₅H₃₅N₃ = 737.91) P-43 m/z= 763.3(C₅₇H₃₇N₃ = 763.94) P-44 m/z = 713.28(C₅₃H₃₅N₃ = 713.88) P-45 m/z= 713.28(C₅₃H₃₅N₃ = 713.88) P-46 m/z = 713.28(C₅₃H₃₅N₃ = 713.88) P-47m/z = 763.3(C₅₇H₃₇N₃ = 763.94) P-48 m/z = 713.28(C₅₃H₃₅N₃ = 713.88) P-49m/z = 687.27(C₅₁H₃₃N₃ = 687.85) P-50 m/z = 687.27(C₅₁H₃₃N₃ = 687.85)P-51 m/z = 661.25(C₄₉H₃₁N₃ = 661.81) P-52 m/z = 737.28(C₅₅H₃₅N₃ =737.91) P-53 m/z = 761.28(C₅₇H₃₅N₃ = 761.93) P-54 m/z = 687.27(C₅₁H₃₃N₃= 687.85) P-55 m/z = 661.25(C₄₉H₃₁N₃ = 661.81) P-56 m/z = 763.3(C₅₇H₃₇N₃= 763.94) P-57 m/z = 564.24(C₄₁H₂₄D₃N₃ = 564.71) P-58 m/z =618.28(C₄₅H₂₂D₇N₃ = 618.79) P-59 m/z = 717.31(C₅₃H₃₁D₄N₃ = 717.91) P-60m/z = 573.3(C₄₁H₁₅D₁₂N₃ = 573.76) P-61 m/z = 672.32(C₄₉H₂₀D₁₁N₃ =672.88) P-62 m/z = 572.29(C₄₁H₁₆D₁₁N₃ = 572.76) P-63 m/z =568.26(C₄₁H₂₀D₇N₃ = 568.73) P-64 m/z = 577.32(C₄₁H₁₁D₁₆N₃ = 577.79)

Reorganization energy (hereinafter, abbreviated as RE) refers to energylost due to a change in molecular structure arrangement when electriccharges (electrons, holes) move. It depends on molecular geometry, andhas a characteristic that the value decreases as the difference betweenthe potential energy surface (hereinafter, abbreviated as PES) in theneutral state and the PES in the charge state decreases. The RE valuecan be obtained by the following formula.

RE _(hole):λ⁺=(E _(NOCE) −E _(COCE))+(E _(CONE) −E _(NONE))

RE _(elec):λ⁻=(E _(NOAE) −E _(AOAE))+(E _(AONE) −E _(NONE))

Each factor can be defined as follows.

-   -   NONE: Neutral geometry of neutral molecules (hereinafter, NO        opt.)    -   NOAE: Anion geometry of a neutral molecule    -   NOCE: Cation geometry of a neutral molecule    -   AONE: Neutral geometry of anion molecule    -   AOAE: Anion geometry of anion molecule (hereinafter, AO opt.)    -   CONE: Neutral geometry of cation molecule    -   COCE: Cation geometry of cation molecule (hereinafter, CO opt.)

Reorganization energy and mobility are in inverse proportion to eachother, and under the condition that they have the same r and T values,the RE value directly affects mobility for each material. The relationbetween RE value and mobility is expressed as follows.

$\mu = {k\frac{r^{2}}{2k_{B}{T/e}}}$$k = {( \frac{4\pi^{2}}{h} )\frac{t^{2}}{\sqrt{4{\pi\lambda}\; k_{B}T}}{\exp\lbrack {- \frac{\lambda}{4k_{B}T}} \rbrack}}$

Each factor can be defined as follows.

-   -   λ: Reorganization energy    -   μ: mobility    -   r: dimer displacement    -   t: intermolecular charge transfer matrix element

From the above formula, it can be seen that the lower the RE value, thefaster the mobility.

The RE value requires a simulation tool that can calculate the potentialenergy according to the molecular structure, and we used Gaussian09(hereafter, G09) and the Jaguar (hereafter, JG) module of SchrodingerMaterials Science. Both G09 and JG are tools to analyze the propertiesof molecules through quantum mechanical (hereafter, QM) calculations,and have the function of optimizing the molecular structure orcalculating the energy for a given molecular structure (single-pointenergy).

The process of calculating QM in molecular structure requires largecomputational resources, and we use two cluster servers for thesecalculations. Each cluster server consists of 4 node workstations and 1master workstation, and each node performed molecular QM calculations byparallel computing through symmetric multi-processing (SMP) using acentral processing unit (CPU) of 36 or more cores.

Using G09, calculate the optimized molecular structure and its potentialenergy (NONE/COCE) in the neutral/charged state required forrearrangement energy. The charge state potential energy (NOCE) of thestructure optimized for the neutral state and the neutral statepotential energy (CONE) of the structure optimized for the charge statewere calculated by changing only the charges to the two optimizedstructures. Then, the rearrangement energy was calculated according tothe following relation.

RE _(charge):λ=(E _(NOCE) −E _(COCE))+(E _(CONE) −E _(NONE))

Because Schrödinger provides a function to automatically perform such acalculation process, the potential energy according to each state wassequentially calculated through the JG module by providing the molecularstructure (NO) of the basic state, and the RE value was calculated.

Meanwhile, the RE values of the present invention calculated accordingto the above calculation method are shown in Table 4 below.

TABLE 4 compound Reorganization energy (RE) P-1 0.157 P-3 0.158 P-250.156 P-26 0.157

Otherwise, the RE values of the comparative compounds calculatedaccording to the calculation method as described above are shown inTable 5 below.

TABLE 5 compound Reorganization energy (RE) comparative compound A 0.299comparative compound B 0.195 comparative compound C 0.191 comparativecompound D 0.261

[Example 1] Red Organic Light Emitting Device (Phosphorescent Host)

An organic electroluminescent device was manufactured according to aconventional method by using the compound obtained through synthesis asa light emitting host material of the emitting layer. First, aN1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4-diamine(abbreviated as 2-TNATA) film was vacuum-deposited on the ITO layer(anode) formed on a glass substrate to form a 60 nm-thick hole injectionlayer, and 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafterabbreviated as -NPD) as a hole transport compound on the hole injectionlayer was vacuum-deposited to a thickness of 60 nm to form a holetransport layer.

As a host on the hole transport layer, the compound (P-1) of the presentinvention represented by Formula (1) was used, and(piq)₂Ir(acac)[bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate] asa dopant material was doped at a weight ratio of 95:5 to deposit anemitting layer to a thickness of 30 nm). Subsequently,(1,1′-bisphenyl)-4-oleato)bis(2-methyl-8-quinolineoleato)aluminum(abbreviated as BAlq) as a hole-blocking layer was vacuum-deposited to athickness of 10 nm, and as an electron transport layer,tris(8-quinolinol)aluminum (abbreviated as Alq3) was deposited to athickness of 40 nm. Then, as an electron injection layer, LiF, an alkalimetal halide, was deposited to a thickness of 0.2 nm, and then, Al wasdeposited to a thickness of 150 nm and used as a cathode to prepare anorganic electroluminescent device.

[Example 2] to [Example 4]

An organic electroluminescent device was prepared in the same manner asin Example 1, except that the compound of the present invention shown inTable 6 was used instead of the compound (P-1) of the present inventionas the host material of the emitting layer.

Example 5

An organic electroluminescent device was manufactured in the same manneras in Example 1, except that the compound (P-1) of the present inventionand the following compound DSNL1 were used as a host material for theemitting layer in a weight ratio of 5:5.

[Example 6] to [Example 24]

An organic electroluminescent device was prepared in the same manner asin Example 1, except that the compounds of the present invention shownin Table 6 and the following compound DSNL1 or DSNL2 were used in aweight ratio of 5:5 instead of the compound (P-1) of the presentinvention as the first compound as the host material of the emittinglayer.

[Comparative Example 1] to [Comparative Example 4]

An organic electroluminescent device was manufactured in the same manneras in Example 1, except that the following Comparative Compounds A to Dwere used as host materials for the emitting layer.

[Comparative Example 5] to [Comparative Example 12]

An organic electroluminescent device was manufactured in the same manneras in Example 1, except that the comparative compound A to thecomparative compound D and the compound DSNL1 or DSNL2 were used in aweight ratio of 5:5 as host materials for the emitting layer.

By applying a forward bias DC voltage to the organic electronic devicesprepared in Examples 1 to 24 and Comparative Examples 1 to 12 preparedin this way, Electroluminescence (EL) characteristics were measured withPR-650 from photo research, and as a result of the measurement, the T95lifetime was measured using a lifetime measuring device manufactured byMcScience at 2500 cd/m² standard luminance. Table 6 below shows thedevice fabrication and evaluation results.

TABLE 6 Current first second Voltage Density Brightness Efficiencycompound compound (v) (mA/cm²) (cd/m²) (cd/A) T (95) comparativecomparative — 6.1 18.9  2500 13.2  85.9 example (1)  compound Acomparative comparative — 6.4 18.2  2500 13.7  86.5 example (2) compound B comparative comparative — 6.8 16.9  2500 14.8  78.6 example(3)  compound C comparative comparative — 5.8 21.7  2500 11.5  55.7example (4)  compound D comparative DSNL1 comparative 5.3 13.4  250018.7 106.4 example (5)  compound A comparative comparative 5.4 12.2 2500 20.5 106.8 example (6)  compound B comparative comparative 5.611.7  2500 21.4 103.2 example (7)  compound C comparative comparative5.1 16.4  2500 15.2 101.2 example (8)  compound D comparative DSNL2comparative 5.2 13.7  2500 18.2 104.2 example (9)  compound Acomparative comparative 5.3 12.7  2500 19.7 106.8 example (10) compoundB comparative comparative 5.5 11.8  2500 21.2 102.5 example (11)compound C comparative comparative 5.0 14.9  2500 16.8  99.9 example(12) compound D example (1)  P-1  — 5.0 10.4  2500 24.1 116.8 example(2)  P-7  — 5.1 10.8  2500 23.2 113.5 example (3)  P-25 — 5.0 10.7  250023.4 117.1 example (4)  P-43 — 5.3 11.3  2500 22.1 109.8 example (5) DSNL1 P-1  4.6 7.5 2500 33.2 142.2 example (6)  P-3  4.6 8.2 2500 30.5133.0 example (7)  P-7  4.7 8.0 2500 31.1 138.5 example (8)  P-17 4.58.5 2500 29.4 132.7 example (9)  P-25 4.6 7.6 2500 32.8 144.7 example(10) P-34 4.8 9.9 2500 25.3 136.7 example (11) P-43 4.9 9.2 2500 27.1131.4 example (12) P-47 4.9 9.5 2500 26.4 129.8 example (13) P-53 4.710.0  2500 25.1 128.9 example (14) P-60 4.8 9.0 2500 27.7 141.8 example(15) DSNL2 P-1  4.5 7.6 2500 32.8 133.8 example (16) P-3  4.4 8.3 250030.0 121.5 example (17) P-7  4.6 8.2 2500 30.5 127.1 example (18) P-174.3 8.6 2500 29.0 121.7 example (19) P-25 4.5 7.7 2500 32.4 135.6example (20) P-34 4.7 10.0  2500 25.1 125.3 example (21) P-43 4.9 9.42500 26.7 120.0 example (22) P-47 4.8 9.5 2500 26.2 119.4 example (23)P-53 4.6 10.4  2500 24.1 119.1 example (24) P-60 4.7 9.2 2500 27.3 129.5

As can be seen from the results in Table 6, when the compound of thepresent invention is used as a material for the emitting layer, it canbe seen that the driving voltage is lowered and the efficiency andlifespan are significantly improved compared to the case of using thecomparative compounds A to D.

It was found that the overall device results were improved whendifferent types of compounds were used through mixing than when theemitting layer compound was used alone. This showed the same trend inthe results of Comparative Compounds A to D and in the device results ofthe present invention.

More specifically, the compound of the present invention has a lower REvalue than the comparative compound. It can be seen that the compound ofthe present invention has a lower RE value only when a plurality ofnaphthyl groups linked to a phenylene group are bonded to a triazine andtheir bonding positions are specific positions described in the presentinvention. Moreover, when a substituent having an excessive number ofcarbon atoms in the substituted configuration is substituted, it isapplied as a factor to increase the RE value.

Since a low RE value is in inverse proportion to mobility, a low REvalue means high mobility, and this mobility means a fast EOD. Overall,it can be seen that the compound of the present invention having a fastEOD value has the characteristics of a fast driving voltage, highefficiency, and long lifespan.

Looking at the compounds of the present invention, it can be seen thatthe RE value has a value in the range of 0.155 to 0.170, and as a commoncharacteristic of these compounds, the driving voltage is pulled and theefficiency is increased.

When the emitting layer was composed of a plurality of mixtures, thecharacteristics were different depending on the type of the firstcompound and the second compound, the device results of the compound ofthe present invention and the comparative compound showed the sametendency. Finally, it can be seen that the driving, efficiency, andlifespan are determined according to the injection characteristics ofholes and electrons into the dopant. In the present invention, it can beseen that through the relationship between the RE value and mobility,the overall driving reduction effect, efficiency and lifetime increaseeffect are brought. Moreover, the present invention is an invention fora compound in which three substituents are introduced into triazine, andwhen a specific substituent is combined, it has a positive effect onoverall mobility and acts as a ratio of a hole to an electron (forexample, energy balance, stability, etc.), showing an overall improvedresult.

Comparing the example compounds, the RE value is determined according tothe type of substituent substituted in the same skeleton, the injectionand migration characteristics of holes and electrons vary according todifferent RE values. Therefore, according to the type of thesubstituent, the compounds of the examples show different propertiesfrom each other.

Although exemplary embodiments of the present invention have beendescribed for illustrative purposes, those skilled in the art willappreciate that various modifications, additions and substitutions arepossible, without departing from the scope and spirit of the inventionas disclosed in the accompanying claims. Therefore, the embodimentdisclosed in the present invention is intended to illustrate the scopeof the technical idea of the present invention, and the scope of thepresent invention is not limited by the embodiment. The scope of thepresent invention shall be construed on the basis of the accompanyingclaims, and it shall be construed that all of the technical ideasincluded within the scope equivalent to the claims belong to the presentinvention.

What is claimed is:
 1. A compound represented by Formula (1):

wherein: 1) Ar₁ and Ar₂ are each independently a C₆-C₁₈ aryl group; or aC₆-C₁₈ aryl group substituted with deuterium; 2) R¹, R², R³, R⁴, R⁵ andR⁶ are the same or different from each other, and independently of eachother are hydrogen or deuterium; and 3) a is an integer of 0 to 7, b isan integer of 0 to
 6. 2. The compound of claim 1, wherein the compoundrepresented by Formula (1) is represented by Formula (1-1) or Formula(1-2):

wherein Ar₁, Ar₂, R¹, R², R³, R⁴, R⁵, R⁶, a and b are the same asdefined in claim
 1. 3. The compound of claim 1, wherein Ar₁ or Ar₂ isrepresented by one of the following compounds:

wherein: 1) R¹, R² and a are the same as defined in claim 1, 2) a′ andb′ are independently of each other an integer of 0 to 5, a″ is aninteger of 0 to 4, and 3) * means the bonding position.
 4. The compoundof claim 1, wherein a reorganization energy value of the compound ofFormula (1) is less than 0.190.
 5. The compound of claim 1, wherein areorganization energy value of the compound of Formula (1) is 0.155 to0.170.
 6. The compound of claim 1, wherein the compound of Formula (1)is selected from the group consisting of compounds P-1 to P-64:


7. An organic electronic element comprising a first electrode, a secondelectrode, and an organic material layer formed between the firstelectrode and the second electrode, wherein the organic material layercomprises an emitting layer, a hole blocking layer and an electrontransport layer, wherein the emitting layer, the hole blocking layer orthe electron transport layer comprises a compound represented by Formula(1) of claim
 1. 8. The organic electronic element of claim 7, whereinthe emitting layer comprises a compound represented by Formula (1). 9.The organic electronic element of claim 7, wherein the emitting layercomprises a first host compound; and a second host compound; wherein thefirst host compound or the second host compound comprises a compoundrepresented by Formula (1).
 10. The organic electronic element of claim7, further comprising a light efficiency enhancing layer formed on onesurface of the first electrode and/or one surface of the secondelectrode not in contact with the organic material layer.
 11. Theorganic electronic element of claim 7, wherein the organic materiallayer includes 2 or more stacks including a hole transport layer, anemitting layer, and an electron transport layer sequentially formed onthe first electrode.
 12. The organic electronic element of claim 11,wherein the organic material layer further comprises a charge generatinglayer formed between the 2 or more stacks.
 13. An electronic devicecomprising: a display device including the organic electronic element ofclaim 7; and a control unit for driving the display device.
 14. Theorganic electronic element of claim 13, wherein the organic electronicelement is any one of an organic electroluminescent device (OLED), anorganic solar cell, an organic photoreceptor (OPC), an organictransistor (organic TFT), and an element for monochromic or whiteillumination.